Allyl bromide → HCID 10956230, compound

HRID 1107280Notes

Reaction equation

HRID 1107280 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[H-].[Na+].[CH2:14](Br)[CH:15]=[CH2:16]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 221092-Bromo-4-nitrophenolHCID 24758Sodium hydride

Product 1

HCID 10956230HCID 10956230, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-4-nitrophenol (9.2 g) was dissolved in dimethylformamide (50 ml) and sodium hydride (2.4 g) was added portionwise. The bright yellow solution was stirred until all effervescence ceased. Allyl bromide (4.7 ml) was added and the resulting solution was heated at 60° C. for 30 minutes. The mixture was cooled, quenched by the dropwise addition of water 30 ml, then diluted with water (500 ml) and extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with sodium hydroxide (2N), water, brine, dried (MgSO4) and evaporated. The residue was purified on silica using 5-10% ethyl acetate in hexane to afford the title compound as a crystalline solid (10 g). 1H NMR (360 MHz, CDCl3) δ 4.72 (2H, d, J=6 Hz), 5.37 (1H, d, J=9 Hz), 5.51 (1H, d, J=15 Hz), 6.94 (1H, d, J=6.5 Hz), 8.18 (1H, dd, J=6.5, 2.6 Hz), 8.47 (1H, J=2.6 Hz).

Workup

  1. temperatureThe mixture was cooled
  2. customquenched by the dropwise addition of water 30 ml
  3. additiondiluted with water (500 ml)
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined organic extracts were washed with sodium hydroxide (2N), water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified on silica using 5-10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c24affb126aa4caaaa3e505acfe08226
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

Loading…